The reductive coupling of 4-bromo-3,3,4,4-tetrafluorobut-1-ene with 2.4 equivalents of various carbonyl compounds proceeded very smoothly in the presence of 2.4 equivalents of MeLi/LiBr-free at -78 °C for two hours, giving the corresponding adducts in high to excellent yields. On the other hand, triethyl(1,1,2,2-tetrafluorobut-3-enyl)silane, which could be prepared by treatment of 4-bromo-3,3,4,4-tetrafluorobut-1-ene and chlorotriethylsilane with magnesium at 0 °C for three hours, reacted with some aldehydes in the presence of 1 mol% of tetrabutylammonium fluoride, the desired adducts being obtained in good to high yields.
cules. -Reductive coupling of bromide (I) with aldehydes, ketones or imines in the presence of MeLi yields the corresponding tetrafluorobutene derivatives. Fluoride-catalyzed addition of silane (X) to carbonyl compounds affords a mixture of the expected alcohol and the corresponding silyl ether, which is desilylated by Bu4NF. -(KONNO*, T.; TAKANO, S.; TAKAHASHI, Y.; KONISHI, H.; TANAKA, Y.; ISHIHARA, T.; Synthesis 2011, 1, 33-44, http://dx.
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